


Office Work

by DanyDamn



Series: The Cupcake Tales [4]
Category: Borderlands (Video Games)
Genre: Anal Sex, Body Doubles, Cunnilingus, Deepthroating, Double Penetration, Explicit Sexual Content, F/M, Female Reader, Fivesome - F/M/M/M/M, Handsome Jack - Freeform, Hotdogging, Multi, NSFW, Oral Sex, Plot What Plot/Porn Without Plot, Porn, Reader-Insert, Sex, Smut, Spitroasting, Threesome - F/M/M, Triple Penetration, Vaginal Sex, absolutely ZERO fluff, enjoy smutters, i felt like going all out sorrynotsorry, if you dont like multi-person porn this fic is not for you, this is all a bunch of porn nonsense, this was pointless but its fun, you - Freeform, youre just gonna enjoy HJ and a few of his body doubles thats it lmao
Language: English
Status: In-Progress
Published: 2019-06-20
Updated: 2019-06-20
Packaged: 2020-05-15 15:04:35
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 3,818
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19298173
Author URL: https://archiveofourown.org/users/DanyDamn/pseuds/DanyDamn
Summary: As an escort you had all sorts of clientele, but when you have the opportunity to get in bed with the universe's most ruthless authoritarian, who were you to decline?Ensue a night you'll probably never be able to burn from your mind.





	Office Work

“Are you sure about this?” You asked, stepping through the deactivated shield, trailing the taller stout male as you made your way into the office. “We could get in trouble.”

The man loosened his tie, a bright piece of Hyperion Yellow, as he approached his desk, plucking a glass of liquor that seemed to appear out of nowhere just for him. “Don’t worry your sweet cheeks sweetcheeks, ain’t no trouble to get into when you’re the guy in charge.” He turned to face you, leaning against the edge of his desk. 

You almost stared in awe as you approached him, Handsome Jack, illuminated by the moon beyond the glass that protected the both of you from the cold vacuum of space, an ethereal glow enveloping his figure. He looked even better in this light than he did at the party, the moon giving way to him like the cosmos themselves were made to make apparent his best features. 

You never once in your life thought this was a place you’d find yourself in. Here, on the night of the famous annual Hyperion Gala, in the space station far above Pandora, in Handsome Jack’s famous office with the man, himself, a hot promise circling the thoughts of the both of you. No, this was definitely what fantasies were made of, and here you were, living it. 

“Hmm, the man in charge…” You drawled, stepping closer to him, falling out of your mild stupor as you decided this was a time best taking advantage of. “I guess that means you have a lot of power around here, huh.” 

You pressed up against him, making sure he could see the way your breasts popped from your dress and squished against his chest. He grinned toothily, clearly enjoying your manner of flirtation. It was, after all, one of the reasons the two of you were up here, alone. 

One would find it intriguing why Jack decided you were best suited for his needs. You were no exception to feeling that intrigue. Honestly, even you were surprised when he approached you. A sea of beautiful women, some more scantily clad than others, and plenty prettier than you, practically throwing themselves at him, and yet you were the one alone with him in his office. 

You couldn’t help but feel a sense of pride at the thought. Obviously none of this meant anything, it was a simple hookup, like any other. You weren’t anything special, you never were, not even now, but what more could a girl do let alone feel in this situation? Anybody in the universe could count themselves lucky if Handsome Jack even showed them a sliver of mercy, but this was an entirely other story. What the two of you were about to do was another kind of privilege. 

Sure, Handsome Jack was rumored a womanizer with absolutely no standards, but you didn’t believe that to hold any merit. He may be the guy who’s dick pops at any sight of a well-rounded ass, but his reasons extended beyond what the rumor implied. That’s just who he was. He liked women. A lot. And of course he had standards. If he didn’t then why would he be standing here in his office with you?

“Yeah cupcake, I’m in charge. Say anything and I’ll make it happen.” He replied with a deeper grin, his arm reaching around to hold your shoulder, squeezing you harder against him. 

”Alright, I’ve got a demand, then.” You lifted a leg, pressing your inner thigh against his hip. 

A tipped eyebrow. “Anything.”

You leaned in close. “I demand that you take off your clothes and introduce me to that famous Handsome Jack cock.” 

“Done.” 

If any rumor about Handsome Jack was true, it was that he was quick. It didn’t take him long to remove his jacket, tie, and dress shirt, three incredibly expensive articles of clothing treated like nothing more than rags tossed to the floor. You admired him as he worked himself free of his confines, his toned muscles glistening from the moonlight. It surprised you how fit this man was. He never seemed to do anything other than crack jokes, shoot people and drink all the time. How he managed to keep his body in such good shape was beyond you. Maybe it was a secret he could share with you. Your own body could use such treatment, too many nights spent drinking with rich buffoons of Pandora taking a bit of a toll on your figure. 

For a moment you almost started to feel insecure about yourself. 

“Admiring the goods?” Jack asked, standing in nothing but his pants now. “My ‘don’t look, please touch’ policy is in effect baby.” 

You approached him again, a finger trailing his chest down to the edge of his pants. “I hope that policy has to do with something a little more than just touching.” 

When you tried to tug his pants down he stopped you. “Ah, ah, ah, sweetcheeks, my policy also includes a strict mutual actions act. Whatever I do you have to do. Now let’s see it.”

You smirked, stepping away again. “You mean something like this?” Shrugging off your straps, the top of your dress fell from your shoulders and hung at your hips, exposing your breasts. 

Jack bobbed his head in approval and pulled you closer to him, hands starting their massage on your chest. Your own hands began to travel his body, exploring every nook and cranny of his toned abs before he leaned down to catch you in a heated kiss. 

Before long, it was easy to detect signs of an erection pressing against your inner thigh. You grinned into his lips and lifted your leg to press against it, prompting him to abandon your breasts and instead take your ass, grinding your body into him. You felt it growing, growing, and Jesus Christ how much more growing was it going to do?

Soon you just had to see for yourself, and the second he spared you for a breath you began unbuckling him while he practically tore your dress apart to be rid of it. When finally he kicked his pants away you stepped back to have a good look. 

He was big. Possibly even too big. And he knew that, if his cocky expression was saying anything.

“What’s the matter kitten, a little too much for ya?” 

You pondered for a moment. “I’m gonna need a little more to drink.” 

With a snap of his fingers Jack somehow made it happen. Whatever system that took care of his drinking habits now catered to you, popping out a nice full glass of something you didn’t care about as long as it did the job. You pressed yourself against the desk, downing the entire glass. When you finally set it down, felt several appendages pressed against you from behind. Jack had taken his place at your ass, hands on your hips, cock between your cheeks, hotdogging you in a lazy thrust. 

He really was huge. Like a big, thick slug it lie on you, heavy and promising. You didn’t believe you’d ever encountered such a creature, but you couldn’t say it didn’t somehow excite you. If there was one rumor about Handsome Jack you were hoping to be true, it was this one. 

You felt his hands trail down your hips to your ass, squeezing both sides to trap his cock in a hot fleshy prison. His thrust quickened a bit, and even you began to move against him. He grunted a little, now pressed fully against you, trapping himself between his stomach and the wet folds of your cunt, which had now become rather slick with wetness. The both of you grinded, breaths quickening and moans escalating. 

Jack continued to grind, leaning forward, one hand tweaking your breast while the other did the same between your legs. You could feel his lips, cool and calculated at the back of your shoulder, leaving a wake of moisture on your skin. Good god, the man knew how to turn a woman on. If you hadn’t already been getting wet at the thought of getting down and dirty with him, this alone would’ve been enough to get you ready. 

When you saw him at the party, a popular figure in the crowd, surrounded by hopeful ladies and businessmen alike, you could tell instantly the type of man he was. Everybody wanted to be his friend, his partner, his lover, and when they didn’t or knew they couldn’t, just wanted to simply be on his good side. When he approached, you pondered which of the roles you could occupy when it came to knowing him. It couldn’t have been the business union; no, you weren’t any kind of executive. Friends was a better shot, but you didn’t see any relationship of the sort between the both of you. As for lover… that was a mildly hopeful venture. The most likely. If you couldn’t possibly be that, then you didn’t see any reason you had to know Handsome Jack at all. 

It was why you welcomed his good graces when he eventually provided his presence. Perhaps it really was your purpose, to be a lover. You were, after all, working in such an occupation. 

Perhaps he sensed it. Perhaps he’d seen and recognized you from the many times he visited your establishment to seek out entertainment of the under-cover kind. It was the only thing you could come up with to explain why he could possibly look at you and make a beeline. It was like you observed: you weren’t throwing yourself at him and you clearly weren’t in his league, so although you were hopeful to finally show Handsome Jack your skills as an escort, didn’t actually understand why he did, eventually look to you for entertainment. 

On the verge of telling him to get started, you felt a poke at your core. As if he was reading your mind, Handsome Jack pulled back and lined himself up, and without a word, slowly slid inside you. He grunted at the tightness, while you gasped through your teeth at the stretching. You were right, he was too big. All too suddenly your doubts clouded your mind as you felt his cock squeeze into you. Perhaps this was a bad idea. 

Despite all that, you didn’t say anything. And with a calloused hand clamped on your shoulder for steadiness, it began. 

Jack hadn’t yet tucked himself in entirely, barely halfway and feeling resistance. Somehow it surprised you that he didn’t right then and there force his entire length to fit. You didn’t take him for the slow kind, but here he was, thrusting shallowly as if in attempt to get your body to adjust to his abnormal size. It was unexpected, but not unappreciated. If anything, it only eased the doubt in your mind about the whole thing. 

It didn’t take too long for your body to accommodate, your cunt relaxing and letting him slide in bit by bit until he was flush against you. He took it as a cue; you were ready. And with that it really began, and right there you remembered why it was that you were looking forward to doing this. It suddenly excited you as his hands took your waist, pulled you away from his cock, and slammed you back onto him. 

A cry left your throat, hands flailing to steady yourself, finding purchase at the edge of the desk he bent you over. Again he did it, grasping, pulling, and slamming, and again you cried out. He picked up the pace, his cock slipping in and out of you with ease, until finally you began to feel the pressure of pleasure coursing through your abdomen. Cries transformed into excited moans, grating pain into rakes of bliss, thrusting into full blown fucking. 

This was what you were here for; bouncing wildly off the cock of the famous Handsome Jack, screaming his name while he pounded you into oblivion. Obviously, you weren’t sure it was even possible to get to this point, but damned if you hadn’t hope for it. Too many rumor’s about the sexual exploits of this stout executive, too many stories from fellow escorts about his god-like skills and far too many unsatisfactory appointments with men who claimed they could live up to expectation. No more.

“Fuck me! Fuck me Handsome Jack! Harder, please, I need more!” You couldn’t stop yourself from crying, not when you felt this man’s enormous appendage rearranging your insides, stuffing you like nothing else had before. 

And suddenly, with a jerk, it wasn’t. 

In a confused haze, you slowly came to realize that Jack had pulled out of you and stepped away, leaving you alone bent over his desk, whimpering pathetically. 

“More, huh? How much more are we talking, here?” Came his sly voice behind you, prompting you to flip yourself over on the desk onto your back, ends of your feet propped up on the edge.

You gave him a desperate look. “Just—more. I-I don’t know.”

“No seriously, you want more? Cuz I can show you more.”

Oh god, it was a trap. He was trying to trick you. He didn’t like you insinuating that his current efforts weren’t enough and he was about to punish you for it, that had to be it. You quickly began to regret even opening your mouth in the first place. 

“I-I guess so..” You said, worrying your bottom lip alongside a mildly terrified gaze. 

Lifting a finger to signal that he needed a moment, your eyes grew a concerned look about them while he turned around, plucking his echo device from it’s place on the desk and dialing a number. He stepped away a few feet, talking in a hushed whisper to keep you out of the loop, and before long, returned, placing back the device. Your eyes followed him as he stepped in front of you again, his rock-hard cock falling against your stomach while he treated you to a sly smirk. 

“What… was that about?” You asked, confused as you’d expected him to have tossed you out of the airlock by now. 

Jack’s smirk only grew. “You’ll find out soon enough, cupcake.” He replied simply, lazily grinding his cock against your abdomen. 

It did nothing to ease your concern, not when he leaned down to treat you to a kiss as his hands plucked at your breasts and his cock teased the sensitive nub between your legs. He was stalling, but for what, you couldn’t say. All you were sure about was that he was up to something, and you couldn’t decide whether you should be excited or even more terrified. 

A ding. Jack pulled away from you a bit, reaching over to his desk to press something on the command panel. Behind him was a flash of light, and as you straightened out, only then did you get a mild idea as to what his plan was.

You really, _really_ , shouldn’t have said something. 

Before your very eyes, stood three other Handsome Jacks. All had identical faces and builds, the only thing differentiating them being the clothes they wore. One had raider’s gear, the other in Jack’s signature outfit, and the third in odd civilian’s clothes. The naked one in front of you stepped forward and gestured at them.

“Gentlemen!” He trilled, “Glad to see you could make it.”

“Um…Jack? ”You spoke up. “What’s… going on. Who are these guys?”

“Ya mean it’s not obvious?” He replied, turning to face you again as his arms swung around two of the duplicates. “These fine men are my body doubles! Who they are doesn’t matter, it’s all about the face. And these particular doubles happen to be my favorite. And they’re here,” he paused as his face darkened into a pointedly evil smirk. “To give you more.” 

You’d figured that out long before he said it, but hearing him admit it made your blood run cold. You visibly gulped, seeing the rest of the Jacks follow the leader in their chilling gaze. Oh god what did you get yourself into.

“Aw, don’t look at us like that cupcake.” The naked Jack said, approaching but stepping around his desk to stand behind you, hands clamped onto your shoulders. “You said you wanted more, didn’t’chya? Well who the hell is Handsome Jack if he can’t deliver upon a lady’s wishes.”

His voice had taken a dark tone, sending a chill down your spine. “I don’t know, Jack… I don’t think I can do this much.”

“Oh that’s just crazy talk! Come on, you’ll enjoy it, I promise. Here, let’s start with my favorite, he’ll get you into the groove.”

With a glance, the Jack in his signature outfit stepped forward, already unzipping his pants and fishing out a cock identical to the original’s. If you were afraid of anything at the moment, it was the idea of all three of these duplicates sharing the same package, in all its size and glory. Used all at once, they were going to tear you apart. 

As if reading your mind and considering your fear, the signature one did something you weren’t expecting. Instead of going for penetration, he got to his knees and simply pressed his mouth to your waiting cunt. In its suddenness your body jerked, not expecting for this specific wave of sensation to course through you. Behind you, you could hear the original Jack’s chuckle while a set of moans began tumbling from your throat, the mouth between your legs unleashing havoc upon your nerves. 

You were mildly aware of one of his hands on your outer thigh, pushing your legs farther apart while you figured his other hand was at his dick, hardening himself while he worked on you. At your shoulders you felt pressure, urging you to lie down on your back. When you did, you were met with the original’s cock, ready and waiting just above your face. Without a thought you opened your mouth and lifted your head, meeting it in a union of flesh and tongue. 

The man at your core hastened his pace, tongue lapping and pushing and thrusting. Your moans grew as a result, finding it difficult to focus at the cock on your mouth while your body reacted to the assault on your nerves. This guy was good, really good. Whoever he was behind the Handsome Jack appearance, the man sure knew how to please a woman. 

Your orgasm was steady approaching, you weren’t sure how much longer you had if he kept this up. While the coil in your stomach tightened, your legs began to squeeze together, hands gripping into the hair of the one responsible for the assault. For a moment you were afraid of suffocating him, your thighs framing his stolen face, but figured he was okay when he made no move to resist. And once you could feel yourself about to peak, found that you didn’t care much, grinding yourself into his eager mouth, your moans a cacophony of pleasure and torture. 

You were acutely aware of the original’s cock in front of your face, but had a hard time keeping your mind on it. It was then that you realized it was moving, at first away from you, but then drilling into your open mouth. With muffled noises you felt only a portion of him slip in, finding resistance because of his size. One of your hands found their way around his base in an attempt to keep him from forcing his entire length down your throat. It was then that your body decided to release. 

In that moment two things happened: Your body seized up, legs locked around the imposter Jack’s head, shaking intensely; while the Jack down your throat had thrusted forward, his entire length slipping inside you, your lips meeting his base. 

It was a second that passed before the men at either sides of you removed themselves, prompting you to turn over and cough in a violent manner over the edge of the desk. You sucked in a few battered breaths, looking up just as the Jack in front of you took your chin and pulled you upwards, meeting you in a sloppy kiss. You took it gratefully, finding it a pleasant chaser to what you had just swallowed.

But it seemed like the pleasantries only lasted mere moments. 

Hoisting you up, Jack’s hands hooked you beneath your knees, guiding your body to meet and sink down on his cock. You fit just right after the first entrance and getting all loosened up from your orgasm, finding it a blessing not to be feeling any pain at this point in time. With where this night was headed, you were going to need all the help you could get.

Hands interlocked at the back of his neck, you kept your mouth on his, a telltale sign that you were ready to proceed. But before he could start bouncing you on top of him like a rubber ball on a bouncy castle, the both of you had to wait a moment before a second Jack came to join you, positioning himself flush behind you. You knew it was coming, and though you weren’t sure you were entirely prepared for it, braced yourself in the most relaxed manner you could, letting the imposter heterochrome fill a second orifice. 

A strained cry left your mouth, removing your face from the Jack in front of you to lay your head back on the shoulder of the Jack behind you. For a moment you hoped the three of you would stay there, waiting a moment to let your body adjust to the two steel rods piercing you like skewers would a marshmallow, but they weren’t going to afford you such a luxury. With a shared glance between the Jacks they began to move, out of sync while they worked to find tandem with their thrusts. 

It took all your willpower not to be split in two, although it certainly felt like it. Every fear that you felt when you first saw the body doubles flash into the room came rushing back to you. Sure you had yet to take any serious injury but the night was still young, there was still plenty to be done and plenty to be afraid of. And as you felt the two cocks inside you find sync in their rhythm, pressing deeper and deeper into you, you had yet to decided if this was a good idea or not. 

It was the dream of many ladies who’d fantasized being with Handsome Jack, but you were first handedly experiencing that fantasy was a _lot_ different than what you were going through now. 

Now you’d have to find out if you were even going to survive the night.

**Author's Note:**

> This was originally supposed to be a one chapter thing, but I already nearly hit 4k words with what I already had and knew this thing wasn't nearly close to being done. I have a problem with experiencing burnout when I write too much on a single chapter so I needed to split things
> 
> but other than that i hope ya'll enjoy this absolute porn nonesense that i wrote on whim because im gross


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